Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 23, Pages 14300-14306Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01908
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Funding
- Samsung Science and Technology Foundation [SSTF-BA1601-10]
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The favorable effect of 2-hydroxyphenyl groups for ketimine formation with benzophenone was demonstrated by combining computational and experimental studies. Although direct imine formation between benzophenone and primary amines is challenging, 2-hydroxybenzophenone or 2,2'-dihydroxybenzophenone was readily used for ketimine formation with various primary alkyl amines and anilines. Measured activation parameters and calculated energy profiles indicated that the 2-hydroxyphenyl group can lower both activation barriers and equilibrium energies by establishing intra-molecular and intermolecular hydrogen-bonding interactions.
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